Heteroarylpyrimidine compound and formulation for controlling harmful organisms

Abstract

wherein, X represents a halogeno group, a substituted or unsubstituted C1-6 alkyl group, or the like; n is an integer ranging from 1 to 3; Z represents an oxygen atom, a sulfur atom, or NR; R represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group; A represents a benzene ring or a 6-membered heteroaryl ring; Ra represents a substituted or unsubstituted C1-6 alkylsulfonyl group; and Rb represents a substituted or unsubstituted C1-6 alkyl group, and the like.

What is claimed is: 
     
         1 . A compound represented by Formula (I), an N-oxide compound thereof, a stereoisomer, a tautomer, a hydrate, or a salt thereof, 
       
         
           
           
               
               
           
         
         wherein 
         X is a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-8 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted 5- to 6-membered heteroaryl group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted 5- to 6-membered heteroaryloxy group, a nitro group, a cyano group, or a group represented by —NR 1 R 2 , 
         each of R 1  and R 2  is independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkyl carbonyl group, or a substituted or unsubstituted C1-6 alkoxy carbonyl group, 
         n is an integer of any one of 1 to 3, 
         Z is an oxygen atom, a sulfur atom or NR, 
         R is a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, 
         A is a benzene ring or a 6-membered heteroaryl ring, 
         R a  is a substituted or unsubstituted C1-6 alkylsulfonyl group, 
         R b  is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkyl carbonyl group, a substituted or unsubstituted C1-6 alkoxy carbonyl group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-8 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted 5- to 6-membered heteroaryl group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted 5- to 6-membered heteroaryloxy group, a nitro group, a cyano group, a group represented by —NR 3 R 4 , a group represented by —C(═O)NR 8 R 9 , a group represented by —C(═NH)R 10 , a group represented by —CR 11 ═N—OR 12 , a group represented by —C(═O)N═S(O) m R 13 , or a group represented by —N═S(O)R 14 R 15 , 
         each of R 3  and R 4  is independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkyl carbonyl group, a substituted or unsubstituted C1-6 alkoxy carbonyl group, an amino group, a group represented by —C(═O)NR 5 R 6 , or a group represented by —C(═NH)R 7 , 
         each of R 5  and R 6  is independently a hydrogen atom, or a substituted or unsubstituted C1-6 alkyl group, 
         R 7  is a C1-6 alkoxy group, or an amino group, 
         each of R 8  and R 9  is independently a hydrogen atom, or a substituted or unsubstituted C1-6 alkyl group, 
         R 10  is a C1-6 alkoxy group, or an amino group, 
         each of R 11  and R 12  is independently a hydrogen atom, or a substituted or unsubstituted C1-6 alkyl group, 
         m is 0 or 1, 
         R 13  is a C1-6 alkyl group, and 
         each of R 14  and R 15  is a C1-6 alkyl group. 
       
     
     
         2 . A formulation for controlling harmful organisms, comprising at least one compound selected from the group consisting of the compounds as recited in  claim 1 , N-oxide compounds thereof, stereoisomers, tautomers, hydrates, and salts thereof, as an active ingredient. 
     
     
         3 . An insecticidal formulation or an acaricidal formulation, comprising at least one compound selected from the group consisting of the compounds as recited in  claim 1 , N-oxide compounds thereof, stereoisomers, tautomers, hydrates, and salts thereof, as an active ingredient. 
     
     
         4 . A formulation for controlling ectoparasites, comprising at least one compound selected from the group consisting of the compounds as recited in  claim 1 , N-oxide compounds thereof, stereoisomers, tautomers, hydrates, and salts thereof, as an active ingredient. 
     
     
         5 . A formulation for controlling endoparasites or for expelling endoparasites, comprising at least one compound selected from the group consisting of the compounds as recited in  claim 1 , N-oxide compounds thereof, stereoisomers, tautomers, hydrates, and salts thereof, as an active ingredient.